alpha-Diphosphopyridine nucleotide

Base Information

• Chemical Name: alpha-Diphosphopyridine nucleotide
• CAS No.: 7298-93-3
• Molecular Formula: C₂₁H₂₇N₇O₁₄P₂
• Molecular Weight: 663.431
• European Community (EC) Number: 230-738-0
• DSSTox Substance ID: DTXSID30858990
• Wikidata: Q27456896
• Mol file: 7298-93-3.mol

Synonyms:7298-93-3;alpha-Diphosphopyridine nucleotide;alpha-Nicotinamide adenine dinucleotide;alpha-nicotinamide adenine dinucleotide,alpha-diphosphopyri;alpha-NAD;Adenine-alpha-nicotinamide dinucleotide;[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5S)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate;DTXSID30858990;CHEBI:183817;Adenine-|A-nicotinamide dinucleotide;alpha-nicotinamide-adenine-dinucleotide;Q27456896;A-NICOTINAMIDE ADENINE DINUCLEOTIDE*CELLCULTURE TE;1-((2S,3R,4S,5R)-5-((((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryloxy)oxidophosphoryloxy)methyl)-3,4-dihydroxytetrahydrofuran-2-yl)-3-carbamoylpyridinium;alpha-Nicotinamide adenine dinucleotide, from Saccharomyces cerevisiae, <1% beta-isomer, >=95%

Chemical Property of alpha-Diphosphopyridine nucleotide

Chemical Property:

• PSA: 340.71000
• LogP: -1.29620
• Storage Temp.: −20°C
• XLogP3: -6
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 18
• Rotatable Bond Count: 11
• Exact Mass: 663.10912256
• Heavy Atom Count: 44
• Complexity: 1120

Purity/Quality:

98%,99%, ^*data from raw suppliers

α-Nicotinamide adenine dinucleotide from Saccharomyces cerevisiae, <1% β-isomer, ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C[N+](=C1)C2C(C(C(O2)COP(=O)([O-])OP(=O)(O)OCC3C(C(C(O3)N4C=NC5=C(N=CN=C54)N)O)O)O)O)C(=O)N
• Isomeric SMILES: C1=CC(=C[N+](=C1)[C@@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)([O-])OP(=O)(O)OC[C@@H]3[C@H]([C@H]([C@@H](O3)N4C=NC5=C(N=CN=C54)N)O)O)O)O)C(=O)N
• Uses: α-Nicotinamide adenine dinucleotide (αNAD) may be used together with other NAD analogues to study the specificity and kinetics of NAD-dependent and NAD-transporting enzymes and proteins, such as NAD-glycohydrolase(s) and the mitochondrial NAD+ transporter in Saccharomyces cerevisiae . α-Nicotinamide adenine dinucleotide has been used in superoxide dismutase activity of seminal plasma samples and in glutathione peroxidase assay of liver, kidney, testes and brain samples.

Technology Process of alpha-Diphosphopyridine nucleotide

There total 4 articles about alpha-Diphosphopyridine nucleotide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 50.0%

3-(aminocarbonyl)-1-[5-O-[[1-(6-amino-9H-purin-9-yl)-1-deoxy-β-D-ribofuranos-5-O-yl]phosphonyloxy(oxylato)phosphinyl]-β-L-ribofuranosyl]pyridinium (865-05-4,144300-52-7) → nicotinamide adenine dinucleotide (53-84-9,7298-93-3,26941-59-3,34469-53-9,58001-39-1,69778-96-7,108646-17-9,108647-57-0,66844-06-2)

Guidance literature:

Rh(bpy)2⁽¹⁺⁾; electrochemical reaction;

Reference yield:

nicotinamide adenine dinucleotide (58-68-4,443892-10-2) → nicotinamide adenine dinucleotide (53-84-9,7298-93-3,26941-59-3,34469-53-9,58001-39-1,69778-96-7,108646-17-9,108647-57-0,66844-06-2)

Guidance literature:

With p-benzoquinone; In water; acetonitrile; at 30 ℃; Rate constant; Mechanism; pH=7.0, with different quinones;

DOI:10.1021/ja00288a035

Reference yield:

C21H28(2)HN7O14P2 (10012-96-1,10021-11-1,18555-06-1) → nicotinamide adenine dinucleotide (53-84-9,7298-93-3,26941-59-3,34469-53-9,58001-39-1,69778-96-7,108646-17-9,108647-57-0,66844-06-2) + C21H26(2)HN7O14P2 (60797-91-3)

Guidance literature:

With 4-methylbenzo-1,2-quinone; In water; at 30 ℃; Rate constant; Mechanism; pH=7.0, with different quinones;

DOI:10.1021/ja00288a035

upstream raw materials:

5'-adenosine monophosphate

3-(aminocarbonyl)-1-[5-O-[[1-(6-amino-9H-purin-9-yl)-1-deoxy-β-D-ribofuranos-5-O-yl]phosphonyloxy(oxylato)phosphinyl]-β-L-ribofuranosyl]pyridinium

C₂₁H₂₈⁽²⁾HN₇O₁₄P₂

nicotinamide adenine dinucleotide

Downstream raw materials:

nicotinamide adenine dinucleotide

cyclic adenosine 5'-diphosphate ribose

2-acetamido-2-deoxy-D-gluconic acid

Refernces

• 1、 Wienkamp, Rainer,Steckhan, Eberhard. "Indirekte elektrochemische Regeneration von NADH mit einem Bipyridin-Rhodium(I)-Komplex als Elektronenuebertraeger". . p. 786. Retrieved 2007/10/02.